Retire With Purpose - The Retirement Podcast
Casey Weade
Whether you are in retirement or have yet to make the transition, The Retire With Purpose podcast is a show designed to help you maximize your financial confidence and elevate your fulfillment in this chapter of life.
Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and Founder of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you've always imagined and deserve.
Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations.
©2024 HOWARD BAILEY FINANCIAL, INC.
Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and Founder of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you've always imagined and deserve.
Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations.
©2024 HOWARD BAILEY FINANCIAL, INC.
Episodes
Mentioned books
Dec 19, 2025 • 31min
539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions
Discover the surprising benefits of capital gains harvesting and why some retirees choose to realize gains instead of losses. Learn about the 0% capital gains bracket and the strategic timing for tax planning around Social Security and RMDs. The discussion dives into whether tax gain harvesting or Roth conversions offer better long-term savings, with insights on the implications of converting IRAs. Tune in for a fresh perspective on navigating taxes to maximize your retirement portfolio.
Dec 12, 2025 • 26min
538: Freedom After 50: Why Enough Is a Mindset, Not a Number
Les McDaniel, a certified retirement coach and financial advisor, joins the discussion on redefining what 'enough' means in retirement. They explore how believing one never has enough can hinder joy, revealing the perils of oversaving and the downsides of the FIRE movement. The conversation shifts to the importance of pursuing curiosity and creativity over constant striving, emphasizing that self-worth should precede financial wealth. Ultimately, they advocate for using money to enable meaningful experiences rather than simply chasing a number.
25 snips
Dec 8, 2025 • 1h 7min
537: The Most Overlooked Elements of a Successful Retirement with Fritz Gilbert
Fritz Gilbert, an award-winning blogger and author of The Retirement Manifesto, shares insights from his six-year retirement journey. He discusses the emotional evolution of retirement, emphasizing the importance of giving yourself permission to spend and enjoy life now rather than later. Fritz reveals how to intentionally reshuffle priorities, avoid the common retirement pitfalls of boredom and identity loss, and maintain fulfillment through continued learning. Plus, he offers unique strategies for financial planning to enhance satisfaction.
21 snips
Dec 5, 2025 • 39min
536: By the Numbers: Cash Out or Hold On? The Retiree's Dilemma
Amid market uncertainty, the focus is on staying invested while navigating cash decisions. The hosts discuss the pitfalls of timing the market and the importance of rebalancing portfolios according to retirement timelines. Psychological stability is evaluated, along with practical strategies for utilizing cash and managing risk. They highlight investor behavior as a key threat and stress reassessing spending goals. Finally, seven actionable tips are offered to guide retirees considering cashing out.
9 snips
Nov 28, 2025 • 30min
535: Freedom After 50: The "Unforgivable Sin" in the Second Half of Life
Les McDaniel, a certified retirement coach and contributor to Retire With Purpose, joins Casey Weade to delve into the complexities of relationships after 50. They explore how our attachment to certainty can hinder deeper connections, especially during family gatherings. Fear’s role in reinforcing rigid beliefs is discussed, along with the importance of empathy and curiosity in fostering open dialogues. Les emphasizes viewing values as flexible filters that encourage growth and understanding, advocating for a humble approach to navigating life's uncertainties.
9 snips
Nov 21, 2025 • 28min
534: By the Numbers: Gold vs. Stocks — What the Data Says About Retirement Portfolios
Dive into the debate of gold versus stocks in retirement portfolios. With gold's recent surge, experts analyze whether it's a worthy investment or merely a fleeting distraction. Historical data reveals how gold stacks up against stocks over the long term. They dissect the role of central banks and the effects of inflation. Practical advice is given on diversifying with gold, advocating for modest allocations to enhance portfolio stability. Tune in for insights that could reshape your retirement strategy!
8 snips
Nov 14, 2025 • 19min
533: By the Numbers: The Case for "Good Enough" — Why Simplicity Often Beats Perfection in Retirement Planning
Striving for the ideal retirement portfolio might be more hindering than helpful. Discover the difference between satisficers, who find joy in simplicity, and maximizers, who search for perfection. Insights from the Bogleheads conference highlight this irony. Learn how prioritizing energy across life roles can lead to balance and happiness. The conversation emphasizes the importance of delegation and offers practical questions to avoid the maximizer trap. Embracing a 'good enough' mindset could be your key to a fulfilling retirement.
43 snips
Nov 10, 2025 • 1h 1min
532: Debunking Advice From Financial "Gurus" to Create An Efficient Retirement Income Plan with David McKnight
David McKnight, a best-selling author and tax strategist, challenges conventional financial wisdom and debunks misleading advice from so-called financial gurus. He explores the psychological appeal of simple guru guidance and its risks, particularly around annuities and withdrawal strategies. McKnight emphasizes the importance of math-based retirement planning and discusses the implications of tax cuts on Roth conversions. With insights on managing longevity risk and the role of insurance, he offers a refreshed perspective on securing a financially sound retirement.
10 snips
Nov 7, 2025 • 26min
531: By the Numbers: Why Retirees Often Spend Too Little, Too Late
New research reveals retirees often under-spend, missing out on their healthiest years. The concept of a 'retirement spending smile' highlights how financial planning can maximize enjoyment in retirement. The hosts also discuss common pitfalls in traditional income strategies and the psychological factors behind spending regrets. Insights into inflation's effects on retirees' investment approaches shed light on balancing risk and security. Exploring gold's role, they analyze its history and relevance, emphasizing thoughtful financial strategies for a fulfilling retirement.
25 snips
Oct 31, 2025 • 27min
530: Freedom After 50: How Challenge Rekindles Purpose in Your Next Chapter
Les McDaniel, a certified retirement coach at Howard Bailey Financial, explores the surprising idea that true fulfillment in retirement comes from embracing challenges, not just relaxation. He discusses how comfort can diminish resilience and emphasizes the importance of 'controlled challenges' in promoting personal growth. Les also highlights insights from ancient wisdom on discomfort and the cultural admiration for resilience. Ultimately, he encourages retirees to engage in small hard choices to discover their core values and leave a meaningful legacy.
